Process for the production of azo dyestuffs on the fiber



Patented-Mala, 1940 UNITED STATES PATENT OFFICE- Heinrich Mhrschei andLudwig Niissler,.l.everkusen, Rhine, and

Wolfgang Alt,

Hans Krzikalla and Ludwigshaien, Rhine, Germany,

assignors to General Aniline & Film Corporation, a. corporation ofDelaware No Drawing. Application March '8,

No. 260,338. in Germany March 10 Claims.

Thepresent invention relates to a process of dyeing mixtures of wool andcellulosic fibers and to fibers dyed according to this process. t

It has been found that mixtures of wool and 1939, Serial mi.- e- -zeiExample 1 10 g. of a mixed fabric consisting of ma, of wool and 30% ofstaple fiber are treated for one g hour at '35- 80" 0., if desired, inthe presence of cellulosic fibers can be uniformly dyed b y apply awetting agent, in a grounding bath, which ing to these mixturesarylamides of 6 sulio 2 t 1 4 f 4 dim mi byhydroxynaphthalene-3-carboxylic acid, which are 1 1 1 derived fromaromatic diamines or polycyclic 5: gfl i g x p i y monoamines anddeveloping them to azo dyestufis W a e o ,P um m with diazo compounds ofaromatic amines on thecarbonate per 1 part naphtha and of m fibers thuspre treated sodium sulfate (bath ratio 1:20). After ground- Arylamidesof the I'nentioned type are com ing the material is squeezed anddeveloped in the densation products of ,6 su1fo 2 hymxynaph cold for 45minutes with a diazo solution prethalene-S-earboxylio acid with, forinstanceldiia? 5 a g 'i g t ted h f amino compounds of benzene andmonoand e eve ope o yemg S I for a] 35 diammes of diphenyl diphemnether,dipheny1 an hour at -90 C. in the presence of a neutral amine,naphthalene,- fiuor ene, carbazole, dizigf or washing agent A yglowishred of phenyleneoxide, benzothiazoleand so on. g mess pmpemes is ObtainThese arylamides of 6-sulfo-2-hydr0xynaph- Example 2thalene-3-carboxyl1c acid are easily soluble in c w. aqueous solutionsof weak alkalis, for instance, of 10 go 8 mixed Ya consisting o 7 0 W001alkali metal carbonates,- ammonia and similar d f aple fi e a o e for anhour compounds; The arylamides go from these soluaft M (3-, if d in theP n of W ttions uniformly on wool and regenerated cels agent in bathwhich o ta pe l ter $5 lulose. On account of the weak alkalinity of the5 8. 0 y p ne-ii' solutions practically no damage i d t th-carboylaminc)-diphenyl (dissolvedwith addition animal fiber of themixture. The development of O S d um r fl fl n 20 of So um te dyestuffson the fiber with diazotized aromatic (bath ratiolfifih Then the yissqueezed d amines is carried out in the usual way. By this developed45 minutes in the 0016 w a m process dyeings of even shades ranging from(11820 S ut -QD pr p from Y 3o orange to black are obtained which-aredistin- 5-chlorobenzene. The aftertreatme S t e guishecl in generalbygood fastness to water, same as described in Example 1. A red of goodrubbing and light. iastness properties lsobtained. I

- The followingv examples illustrate the invention In the followingtable; further dyeings obtainwithout, however, restricting it thereto.able inthe same way are arranged.

Azo component Diazo component Shade 4,4-dia": 1i -2"-h (nhthal awammgydiillllegyll y oxynap one 3 carboyl l-ainino-a-chlorobenzenel JStrongly yellowishred 40 Do 1-methyl-2-amino-4-chlorobenzene 1 0-.

1-methyl-2-amino-5-chlorobenzene Yell0wish red. D 0 ..l2-amhio+chloro-diphenylethcr Do.3,3-d1methoxy-4,4-d1;(6-sulfo-2"hydroxynaphthalene-.l-mothyl-z-aminol-chlorobenwne Strongly reddish brown.3"-carboylamino)-diphenyl.,

Do 1-amino-2-chlorobenzena Reddish brown.

' 1-methyl-2-amino-4-nitrobenzene Fullred brown.i-amino-4-methory-diphenylamine. Black. a ht one. I t, l,id(6eulfo-2hyd!oxynaphthalene-y-carboylaminoy l-metnoxy-z-amlnor'i-chlorobenwne.;Reddisli Bordeaux. 61126116. Do .1 '1-methoxy-2-amino-5-nitrobonzenoBrownishred bordeaux.

Do 4-ammo-4' 1nethoxy-dipnenylaniincm Black- 42-(6'-sulfo-2-hydroxynaphthalene-3'-carboylamino)-l-amino-z-chlorobenzenafli Scarlet. 50

naphthalene. f c Dc. A l-amlno-3-chlorobenzene .Do.

Do. l-methyl-2-amino-4-chlorobenzcne Red. 4o sgt-hydroxynsphthalene-3'-carboylamino)-1-trifluoromethyl-3-amino-4-chlorobenmne Reddish orange. 1 1 )ol-omino-a-chlorobenzene Scarlet. 65 .Do... 1,:diethoxy-Zmnino-b-bencoylaminobenzene Reddish black.

' ponents Azo component Dluo component Shade2-[4-(6-suiio-2-hydroxynaphthalene-3"-carboyl-trifluoromethyl-B-amlno-4-chlorobenzeneReddlsh orange.

lamino)-phenyl] o-methyl-benzothiazol.

Do l-methyl-Z-omino-B-chlorobenzene Scarlet. Dnl-methoxy-2-amino-4-chlorobenzene. Red. Dol-methoxy-Z-emlno-t-nitrobenaene. Strongly bluish red. Do4-cmino-4-methoxy-diphenylamine m. Black. 2, 2'-dlchloro-4,4'-dl-(6-sulio-2-hydroxynaphthalenel-amino-Zi-chlorobenzenc Stronglyreddish orange.

3-carboylamlno)-diphenyl.

Do l-amino-Z-methyl-i-chlorobenzene Red.4,4-di-(6-sulfo-2"-hydroxynaphthalene-3"-carboylamil-amino-2-methyl4l-chlorobenzeneYellowish scarlet.

no)-dlphenylmethane.

Do l-emino-2-methoxy-benzene-B-auliodiethylamide-.- Yellowish red. 3,3-;li)(6"-suliifi;i2 -hydroxynaphthalenee carboylaml-I-amino-Z-methoxy-B-chlorobenzcne; Bluish red.

no enzan e.

Do l-amino-Z-methyl+chlorobenzene .L Strongly yellowish rod.2,4'-dit-i(16'gsullo-zhydroxynaphthalene-3"-carboylamil-amino-2-methyl-4-chlorobenacne Do.

no p any o a-amino 4-methoxy-dlphenylamlne Greenish dark blue.4,4'-di-(6-sulio-2"-hydroxynaphthalene-3"-carboylamil-amino-B-chlorobenzeneReddish orange.

no)diphenyl-3-sulronic acid.4,44S1li,(6"-sugo-2"-hydroxynaphthalene-lW-carboylami-1-emino-2,6-dichlorobenzene D- no enzop enone.4,4'-di-(6"-sulio-2"-hydroxynaphthalene-.'i-carboylamil-eml'no-2-chlorobenzenoDo.

no)-diphenyl-ether.

Do l-amlno2-methoxy-4-nitrobenzene Brownian red.2-nitro-4,4'-di-(6-sullo-2"-hydroxynaphthalene -3"-4-amiuo-4-meth0xy-diphenylamine Bluish black.

carboylamino)-diphenyl.

Do l-emino-Z-methyl-lichlorobenzene Scarlet.2,2'-dimethyl-4,4"-di-(6"sulio-2"-hydroxy-naphthalenel-amlnoQ-methyl-3-chlorobenzeneYellowish scarlet.

3"-carboylamino)-diphenyl-methane.

Do l-amino-2-methoxy-5-chlorobenzene Red. 2,2'-dichloro-4,4'-dl-6-sullo-2"-hydroxynaphthalenel-amlno-2,5-dichloro-benmne Yellowishscarlet.

3"-carboylamlno) phenylmethane. Do l-amino-2-methyl-4-chlorobensene Red.4,3-di-(6-sulio-2"-hydroxynaphtha1ene-3"-carboyl-1-amlno-2-meth0xy-5-chlorobenzene Red bordeaux.

amino)-benzanilide.

o l-amino-2-chlorobenzene Yellowish scarlet.l-E6-sulio-2-hydroxynaphthalene-3-carboylamln0)'3-1-amino-2,6-dichloro-benzene Orange.

b2: hydroxy 3 methyl 5 chlorobenzoylamino nzene. Do1-amlno-2-methoxy-4-bcnzoylamino-5-mothyl-ben- Blulsh bordeeux.

zone. D0 4,4'-dlchlor0-2-aminodiphenylether Yellowish red.

We claim: is derived from bi-cyclic diamines the two nuclei 1. In-theprocess of producing azo dyestufis on mixtures consisting of wool-andregenerated cellulose by combining coupling components and diazocompounds on the fibers, the modification which comprises employing ascoupling components 6 sulto-2-hydroxynaphthalene-3-carboyl-arylamidesthe arylamide portion 01 which is derived from the group consisting ofaromatic diamines and polycyclic monamines and applying these componentsfrom a neutral to weakly alkaline bath.

2. In the process of producing azo dyestuffs on mixtures consisting ofwool and regenerated cellulose by combining coupling components anddiazo compounds on the fibers, the modification which comprisesemploying as coupling components 6sulfo-2-hydroxynaphthalene-3-carboyl-arylamides the aryiamide portion ofwhich is derived from aromatic diamines and applying these componentsfrom a neutral to weakly alkaline bath.

3. In the process of producing azo dyestuffs on mixtures consisting ofwool and regenerated cellulose by combining coupling components anddiazo compounds-on the fibers, the modification which comprisesemploying as coupling com- 6sulfo-2-hydroxynaphthalene-3-carboyl-arylamides the arylamide portion ofwhich is derived from bi-cyclic diamines and applyingv these componentsfrom a neutral to weakly alkaline bath.

4. 'In the process of producing azo dyestuffs on mixtures consisting ofwool and regenerated cellulose by combining coupling components anddiazo compounds on the fibers, the modification .which comprisesemploying as. coupling components 6sulfo-2-hydroxynaphthalene-3-carboyl-arylamides the arylamide portion ofwhich being connected by one of the group consisting of the diphenyllinkage -0', CO-. CH2--, -NH-, CO.NH-- and HN.CO.NH and applying thesecomponents from a neutral to weakly alkaline bath.

5. In the process of producing azo dyestufis on lulose by combiningcoupling components and diazo compounds on the fibers, the modificationwhich comprises employing 2.2'-dichloro-4.4'-di- (6"-sulto-2'-hydroxynaphthalene 3"- carboylamino) -diphenyl-methane and applying thesame from a neutral to weakly alkaline bath.

7. Mixtures consisting of wool and regenerated cellulose dyed accordingto a process as claimed in claim 1.

8. Mixtures consisting of wool and regenerated cellulose dyed accordingto a process as claimed in claim 4. I

9. Mixtures consisting of wool and regenerated cellulose dyedaccordingto a process as claimed in claim 5. v

10. Mixtures consisting of wool and'regenerated cellulose dyed accord nsto a process as claimed in claim 6. I I

i HEINRICH MORSCI-IEL.

' LUDWIG Ntissnna.

HANS WOLFGANG ALT.

